Biomimetic synthesis and stereostructure of K-13, a novel inhibitor of angiotensin I converting enzyme

Abstract

A novel inhibitor of angiotensin I converting enzyme (K-13) has been synthesized from N-acetyl-3,5-dichloro-L-tyrosyl-O-benzyl-L-tyrosyl-3,5-diiodo-L-tyrosine methyl ester, whose oxidation with thallium trinitrate (TTN) as a key step followed by zinc reduction affords the corresponding diphenyl ether with the same heterocyclic skelton as that of K-13, indicating that K-13 is biosynthesized from three molecules of L-tyrosine.